NPASS Compound

Structure

NPC471684 OpenBabel07101718202D 34 38 0 0 1 0 0 0 0 0999 V2000 4.2174 -3.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2285 -1.1200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2758 -1.3225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 1.8175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2863 1.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5910 -0.1355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8711 0.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 -2.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -3.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8435 1.4610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2285 0.3277 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5305 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5767 -0.3962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7888 0.9686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6870 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 -0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8435 2.4349 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 0.4870 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -4.3829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2174 -1.4610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3740 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7415 1.1711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 7 8 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 29 1 0 0 0 0 15 22 1 0 0 0 0 15 24 1 1 0 0 0 16 23 1 0 0 0 0 16 27 1 6 0 0 0 17 7 1 1 0 0 0 17 22 1 0 0 0 0 17 33 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 23 34 1 0 0 0 0 24 6 1 1 0 0 0 24 33 1 0 0 0 0 25 26 1 1 0 0 0 25 28 1 0 0 0 0 26 10 1 1 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.16
Volume:	485.451
LogP:	5.812
LogD:	3.896
LogS:	-4.3
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	5.912
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891
MDCK Permeability:	1.782431354513392e-05
Pgp-inhibitor:	0.715
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421
Plasma Protein Binding (PPB):	100.59776306152344%
Volume Distribution (VD):	2.084
Pgp-substrate:	2.662489891052246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.324
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.509
CYP2D6-inhibitor:	0.173
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.71
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	6.29
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.448
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.647
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.43
Carcinogencity:	0.389
Eye Corrosion:	0.004
Eye Irritation:	0.703
Respiratory Toxicity:	0.975

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC471684

Natural Product ID:	NPC471684
*Common Name:**	Napyradiomycin Cnq525.510B
IUPAC Name:	(3R,4aR,10aS)-3,4a-dichloro-6,8-dihydroxy-2,2,7-trimethyl-10a-[[(1R,3S,4S)-2,2,4-trimethyl-7-oxabicyclo[2.2.1]heptan-3-yl]methyl]-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	NLSPRIUKOHATQS-VCQHOALXSA-N
Standard InCHI:	InChI=1S/C26H32Cl2O6/c1-12-14(29)9-13-18(19(12)30)21(32)25(28)11-16(27)23(4,5)34-26(25,20(13)31)10-15-22(2,3)17-7-8-24(15,6)33-17/h9,15-17,29-30H,7-8,10-11H2,1-6H3/t15-,16+,17+,24-,25-,26-/m0/s1
SMILES:	Oc1cc2c(c(c1C)O)C(=O)[C@@]1([C@@](C2=O)(C[C@@H]2[C@]3(C)CC[C@H](C2(C)C)O3)OC([C@@H](C1)Cl)(C)C)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104839
PubChem CID:	76324767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32475	actinomycete sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24328269]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	17000.0	nM	PMID[481036]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC471684 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	1727
0.2-0.3	3416
0.3-0.4	9345
0.4-0.5	11487
0.5-0.6	6494
0.6-0.7	8709
0.7-0.8	1053
0.8-0.85	11
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC471686
0.9394	High Similarity	NPC108948
0.9273	High Similarity	NPC311679
0.9273	High Similarity	NPC301846
0.9157	High Similarity	NPC131078
0.9048	High Similarity	NPC184518
0.8869	High Similarity	NPC73544
0.8757	High Similarity	NPC471685
0.8728	High Similarity	NPC158699
0.8324	Intermediate Similarity	NPC316262
0.8324	Intermediate Similarity	NPC314653
0.8161	Intermediate Similarity	NPC470563
0.814	Intermediate Similarity	NPC470559
0.8136	Intermediate Similarity	NPC313717
0.8136	Intermediate Similarity	NPC315306
0.8103	Intermediate Similarity	NPC470561
0.8092	Intermediate Similarity	NPC313368
0.8057	Intermediate Similarity	NPC471687
0.8012	Intermediate Similarity	NPC471906
0.8	Intermediate Similarity	NPC475106
0.7978	Intermediate Similarity	NPC475656
0.7978	Intermediate Similarity	NPC475148
0.7955	Intermediate Similarity	NPC100849
0.7944	Intermediate Similarity	NPC475080
0.7933	Intermediate Similarity	NPC474004
0.7933	Intermediate Similarity	NPC470562
0.7919	Intermediate Similarity	NPC470564
0.7917	Intermediate Similarity	NPC470570
0.7898	Intermediate Similarity	NPC245122
0.7892	Intermediate Similarity	NPC474961
0.7892	Intermediate Similarity	NPC308572
0.7892	Intermediate Similarity	NPC135524
0.7889	Intermediate Similarity	NPC470560
0.787	Intermediate Similarity	NPC5568
0.7857	Intermediate Similarity	NPC34482
0.7857	Intermediate Similarity	NPC474630
0.7831	Intermediate Similarity	NPC204045
0.7831	Intermediate Similarity	NPC305845
0.7824	Intermediate Similarity	NPC94781
0.7811	Intermediate Similarity	NPC136878
0.7803	Intermediate Similarity	NPC472211
0.7798	Intermediate Similarity	NPC244691
0.7798	Intermediate Similarity	NPC48762
0.779	Intermediate Similarity	NPC118128
0.7778	Intermediate Similarity	NPC474310
0.7778	Intermediate Similarity	NPC120171
0.7771	Intermediate Similarity	NPC196448
0.7771	Intermediate Similarity	NPC181560
0.7771	Intermediate Similarity	NPC169452
0.7765	Intermediate Similarity	NPC125465
0.7735	Intermediate Similarity	NPC470565
0.7733	Intermediate Similarity	NPC470568
0.7727	Intermediate Similarity	NPC472617
0.7727	Intermediate Similarity	NPC239118
0.7727	Intermediate Similarity	NPC218818
0.7725	Intermediate Similarity	NPC110810
0.7719	Intermediate Similarity	NPC112816
0.7714	Intermediate Similarity	NPC280497
0.7711	Intermediate Similarity	NPC138099
0.7711	Intermediate Similarity	NPC242994
0.7711	Intermediate Similarity	NPC103337
0.7711	Intermediate Similarity	NPC114620
0.7711	Intermediate Similarity	NPC190457
0.7705	Intermediate Similarity	NPC264922
0.7697	Intermediate Similarity	NPC471905
0.7692	Intermediate Similarity	NPC169018
0.7692	Intermediate Similarity	NPC474857
0.7692	Intermediate Similarity	NPC193703
0.7692	Intermediate Similarity	NPC29932
0.7692	Intermediate Similarity	NPC21599
0.7688	Intermediate Similarity	NPC470675
0.7688	Intermediate Similarity	NPC473131
0.7688	Intermediate Similarity	NPC470569
0.7684	Intermediate Similarity	NPC470810
0.7684	Intermediate Similarity	NPC472618
0.768	Intermediate Similarity	NPC54903
0.768	Intermediate Similarity	NPC286074
0.7679	Intermediate Similarity	NPC193555
0.7676	Intermediate Similarity	NPC70318
0.7674	Intermediate Similarity	NPC44378
0.7674	Intermediate Similarity	NPC280753
0.767	Intermediate Similarity	NPC272196
0.767	Intermediate Similarity	NPC158542
0.767	Intermediate Similarity	NPC474637
0.7667	Intermediate Similarity	NPC475109
0.7654	Intermediate Similarity	NPC476822
0.7647	Intermediate Similarity	NPC28632
0.7644	Intermediate Similarity	NPC470340
0.7644	Intermediate Similarity	NPC154683
0.7644	Intermediate Similarity	NPC40356
0.7644	Intermediate Similarity	NPC87708
0.764	Intermediate Similarity	NPC117985
0.7637	Intermediate Similarity	NPC277865
0.7636	Intermediate Similarity	NPC191976
0.7636	Intermediate Similarity	NPC254847
0.7633	Intermediate Similarity	NPC159721
0.763	Intermediate Similarity	NPC147735
0.7627	Intermediate Similarity	NPC4950
0.7624	Intermediate Similarity	NPC193222
0.7619	Intermediate Similarity	NPC472603
0.7616	Intermediate Similarity	NPC142846
0.7614	Intermediate Similarity	NPC477674
0.7611	Intermediate Similarity	NPC472049
0.7611	Intermediate Similarity	NPC477834
0.7605	Intermediate Similarity	NPC143438
0.7602	Intermediate Similarity	NPC202112
0.7602	Intermediate Similarity	NPC51513
0.76	Intermediate Similarity	NPC312482
0.76	Intermediate Similarity	NPC477669
0.76	Intermediate Similarity	NPC218870
0.76	Intermediate Similarity	NPC470408
0.76	Intermediate Similarity	NPC182921
0.76	Intermediate Similarity	NPC474824
0.7598	Intermediate Similarity	NPC473022
0.7594	Intermediate Similarity	NPC470332
0.759	Intermediate Similarity	NPC53001
0.759	Intermediate Similarity	NPC53414
0.759	Intermediate Similarity	NPC53206
0.7588	Intermediate Similarity	NPC42540
0.7588	Intermediate Similarity	NPC151607
0.7586	Intermediate Similarity	NPC232645
0.7586	Intermediate Similarity	NPC230848
0.7586	Intermediate Similarity	NPC478148
0.7586	Intermediate Similarity	NPC477672
0.7586	Intermediate Similarity	NPC477673
0.7586	Intermediate Similarity	NPC205918
0.7586	Intermediate Similarity	NPC72958
0.7581	Intermediate Similarity	NPC473607
0.7581	Intermediate Similarity	NPC473729
0.7571	Intermediate Similarity	NPC282390
0.7571	Intermediate Similarity	NPC197326
0.7571	Intermediate Similarity	NPC201127
0.7571	Intermediate Similarity	NPC281137
0.7571	Intermediate Similarity	NPC472404
0.7569	Intermediate Similarity	NPC85047
0.7569	Intermediate Similarity	NPC476255
0.7569	Intermediate Similarity	NPC53640
0.7569	Intermediate Similarity	NPC17274
0.7569	Intermediate Similarity	NPC62444
0.7569	Intermediate Similarity	NPC476056
0.7569	Intermediate Similarity	NPC120857
0.7568	Intermediate Similarity	NPC472661
0.7568	Intermediate Similarity	NPC98943
0.7568	Intermediate Similarity	NPC312630
0.7568	Intermediate Similarity	NPC324220
0.7566	Intermediate Similarity	NPC474499
0.756	Intermediate Similarity	NPC472600
0.756	Intermediate Similarity	NPC156872
0.756	Intermediate Similarity	NPC472601
0.7558	Intermediate Similarity	NPC312929
0.7558	Intermediate Similarity	NPC118027
0.7558	Intermediate Similarity	NPC190648
0.7558	Intermediate Similarity	NPC289042
0.7558	Intermediate Similarity	NPC476821
0.7558	Intermediate Similarity	NPC126767
0.7558	Intermediate Similarity	NPC245584
0.7558	Intermediate Similarity	NPC56433
0.7557	Intermediate Similarity	NPC314257
0.7557	Intermediate Similarity	NPC478221
0.7557	Intermediate Similarity	NPC477687
0.7557	Intermediate Similarity	NPC477671
0.7557	Intermediate Similarity	NPC478133
0.7556	Intermediate Similarity	NPC109180
0.7554	Intermediate Similarity	NPC469393
0.7554	Intermediate Similarity	NPC470333
0.7545	Intermediate Similarity	NPC87723
0.7544	Intermediate Similarity	NPC470674
0.7544	Intermediate Similarity	NPC470673
0.7544	Intermediate Similarity	NPC117716
0.7543	Intermediate Similarity	NPC268992
0.7543	Intermediate Similarity	NPC51824
0.7543	Intermediate Similarity	NPC470338
0.7543	Intermediate Similarity	NPC113608
0.7543	Intermediate Similarity	NPC470337
0.7543	Intermediate Similarity	NPC180944
0.7542	Intermediate Similarity	NPC476929
0.7541	Intermediate Similarity	NPC477571
0.7541	Intermediate Similarity	NPC477572
0.7541	Intermediate Similarity	NPC477573
0.753	Intermediate Similarity	NPC474311
0.7529	Intermediate Similarity	NPC290954
0.7529	Intermediate Similarity	NPC255641
0.7529	Intermediate Similarity	NPC471731
0.7529	Intermediate Similarity	NPC202595
0.7529	Intermediate Similarity	NPC280295
0.7529	Intermediate Similarity	NPC294646
0.7529	Intermediate Similarity	NPC143898
0.7529	Intermediate Similarity	NPC354984
0.7528	Intermediate Similarity	NPC125969
0.7528	Intermediate Similarity	NPC40583
0.7527	Intermediate Similarity	NPC470334
0.7527	Intermediate Similarity	NPC233978
0.7527	Intermediate Similarity	NPC246877
0.7527	Intermediate Similarity	NPC476459
0.7526	Intermediate Similarity	NPC313386
0.7515	Intermediate Similarity	NPC202225
0.7515	Intermediate Similarity	NPC166480
0.7515	Intermediate Similarity	NPC187843
0.7515	Intermediate Similarity	NPC282780
0.7515	Intermediate Similarity	NPC246638

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC471684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	951
0.2-0.3	1955
0.3-0.4	3189
0.4-0.5	1868
0.5-0.6	625
0.6-0.7	205
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7636	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6959	Discontinued
0.7341	Intermediate Similarity	NPD2534	Approved
0.7341	Intermediate Similarity	NPD2532	Approved
0.7341	Intermediate Similarity	NPD2533	Approved
0.7283	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD6784	Approved
0.7211	Intermediate Similarity	NPD6785	Approved
0.7207	Intermediate Similarity	NPD7819	Suspended
0.7189	Intermediate Similarity	NPD7473	Discontinued
0.7182	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2800	Approved
0.7043	Intermediate Similarity	NPD2403	Approved
0.7039	Intermediate Similarity	NPD4380	Phase 2
0.7033	Intermediate Similarity	NPD3882	Suspended
0.7027	Intermediate Similarity	NPD6232	Discontinued
0.7011	Intermediate Similarity	NPD5494	Approved
0.6995	Remote Similarity	NPD8150	Discontinued
0.6977	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6599	Discontinued
0.6935	Remote Similarity	NPD5710	Approved
0.6935	Remote Similarity	NPD5711	Approved
0.6919	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1549	Phase 2
0.6897	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1934	Approved
0.6868	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD1470	Approved
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6559	Discontinued
0.6821	Remote Similarity	NPD1510	Phase 2
0.6818	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8320	Phase 1
0.6814	Remote Similarity	NPD8319	Approved
0.6811	Remote Similarity	NPD3749	Approved
0.6802	Remote Similarity	NPD1607	Approved
0.6802	Remote Similarity	NPD6651	Approved
0.6784	Remote Similarity	NPD6535	Approved
0.6784	Remote Similarity	NPD6534	Approved
0.6784	Remote Similarity	NPD943	Approved
0.6782	Remote Similarity	NPD5406	Approved
0.6782	Remote Similarity	NPD5408	Approved
0.6782	Remote Similarity	NPD5404	Approved
0.6782	Remote Similarity	NPD5405	Approved
0.6772	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6166	Phase 2
0.6766	Remote Similarity	NPD7699	Phase 2
0.6766	Remote Similarity	NPD7700	Phase 2
0.6765	Remote Similarity	NPD7435	Discontinued
0.676	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5844	Phase 1
0.6735	Remote Similarity	NPD8434	Phase 2
0.6721	Remote Similarity	NPD7411	Suspended
0.6703	Remote Similarity	NPD3226	Approved
0.6702	Remote Similarity	NPD3818	Discontinued
0.67	Remote Similarity	NPD6780	Approved
0.67	Remote Similarity	NPD4360	Phase 2
0.67	Remote Similarity	NPD6781	Approved
0.67	Remote Similarity	NPD6782	Approved
0.67	Remote Similarity	NPD6776	Approved
0.67	Remote Similarity	NPD6778	Approved
0.67	Remote Similarity	NPD6779	Approved
0.67	Remote Similarity	NPD6777	Approved
0.67	Remote Similarity	NPD4363	Phase 3
0.6686	Remote Similarity	NPD2796	Approved
0.6686	Remote Similarity	NPD1240	Approved
0.6684	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7696	Phase 3
0.6683	Remote Similarity	NPD7697	Approved
0.6683	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7871	Phase 2
0.665	Remote Similarity	NPD7870	Phase 2
0.6649	Remote Similarity	NPD5761	Phase 2
0.6649	Remote Similarity	NPD7251	Discontinued
0.6649	Remote Similarity	NPD5760	Phase 2
0.6649	Remote Similarity	NPD2801	Approved
0.6631	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1512	Approved
0.6627	Remote Similarity	NPD1201	Approved
0.6615	Remote Similarity	NPD7808	Phase 3
0.6613	Remote Similarity	NPD3817	Phase 2
0.6611	Remote Similarity	NPD6799	Approved
0.6598	Remote Similarity	NPD6797	Phase 2
0.6597	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6234	Discontinued
0.6596	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4361	Phase 2
0.6584	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7768	Phase 2
0.6578	Remote Similarity	NPD4967	Phase 2
0.6578	Remote Similarity	NPD4966	Approved
0.6578	Remote Similarity	NPD4965	Approved
0.6571	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7874	Approved
0.6556	Remote Similarity	NPD3300	Phase 2
0.6555	Remote Similarity	NPD7701	Phase 2
0.6554	Remote Similarity	NPD2346	Discontinued
0.6546	Remote Similarity	NPD7074	Phase 3
0.654	Remote Similarity	NPD7801	Approved
0.6532	Remote Similarity	NPD6663	Approved
0.6531	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7228	Approved
0.6528	Remote Similarity	NPD3751	Discontinued
0.6526	Remote Similarity	NPD1247	Approved
0.6524	Remote Similarity	NPD5402	Approved
0.6524	Remote Similarity	NPD8151	Discontinued
0.6519	Remote Similarity	NPD1511	Approved
0.6503	Remote Similarity	NPD920	Approved
0.6497	Remote Similarity	NPD8312	Approved
0.6497	Remote Similarity	NPD2935	Discontinued
0.6497	Remote Similarity	NPD8313	Approved
0.6495	Remote Similarity	NPD6020	Phase 2
0.6495	Remote Similarity	NPD7054	Approved
0.6474	Remote Similarity	NPD3764	Approved
0.6464	Remote Similarity	NPD7236	Approved
0.6462	Remote Similarity	NPD7472	Approved
0.6459	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3926	Phase 2
0.6457	Remote Similarity	NPD230	Phase 1
0.6447	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3750	Approved
0.6443	Remote Similarity	NPD7799	Discontinued
0.6429	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD919	Approved
0.6418	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD37	Approved
0.641	Remote Similarity	NPD7286	Phase 2
0.6409	Remote Similarity	NPD6190	Approved
0.6407	Remote Similarity	NPD3019	Approved
0.6407	Remote Similarity	NPD2932	Approved
0.6406	Remote Similarity	NPD7229	Phase 3
0.6395	Remote Similarity	NPD5736	Approved
0.6393	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1465	Phase 2
0.6379	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7239	Suspended
0.6369	Remote Similarity	NPD2344	Approved
0.6369	Remote Similarity	NPD1471	Phase 3
0.6364	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4628	Phase 3
0.6354	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD8366	Approved
0.6347	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5953	Discontinued
0.6344	Remote Similarity	NPD7458	Discontinued
0.6344	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6212	Phase 3
0.6324	Remote Similarity	NPD6213	Phase 3
0.6324	Remote Similarity	NPD5403	Approved
0.6324	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3787	Discontinued
0.6316	Remote Similarity	NPD6823	Phase 2
0.6313	Remote Similarity	NPD1551	Phase 2
0.6306	Remote Similarity	NPD8491	Approved
0.6304	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD4914	Approved
0.6298	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD1243	Approved
0.6298	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7003	Approved
0.6264	Remote Similarity	NPD8166	Discontinued
0.6257	Remote Similarity	NPD2799	Discontinued
0.6238	Remote Similarity	NPD4387	Approved
0.6238	Remote Similarity	NPD4386	Approved
0.6231	Remote Similarity	NPD7240	Approved
0.623	Remote Similarity	NPD2309	Approved
0.6229	Remote Similarity	NPD4625	Phase 3
0.6219	Remote Similarity	NPD8407	Phase 2
0.6216	Remote Similarity	NPD5401	Approved
0.6213	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4954	Approved
0.62	Remote Similarity	NPD4955	Approved
0.62	Remote Similarity	NPD5028	Approved
0.62	Remote Similarity	NPD36	Approved
0.62	Remote Similarity	NPD5034	Approved
0.62	Remote Similarity	NPD5026	Approved
0.6199	Remote Similarity	NPD7907	Approved
0.6196	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD1164	Approved
0.6183	Remote Similarity	NPD6273	Approved
0.6172	Remote Similarity	NPD5544	Approved
0.6169	Remote Similarity	NPD5035	Approved
0.6167	Remote Similarity	NPD3748	Approved
0.6158	Remote Similarity	NPD5038	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data